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Winery Hotels in Downtown Chicago

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Featured Downtown Chicago Winery Hotels

Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, Chicago
4 out of 5
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...
Club Quarters Hotel, Central Loop, Chicago
See all 1,621 properties in Downtown Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Downtown Chicago Winery Hotels

Looking for a glass (more than) half full kind of experience on your last-minute getaway to Downtown Chicago? You can’t get more cup runneth over than booking a sip-filled stay at winery hotels. The only thing left to do? Get ready to pop bottles on bubbly good times.

Cheers to Good Deals

When it comes to the best places to stay in Downtown Chicago, winery hotels definitely come out on top. And while you may think you’ll have to blow stacks of cash on your perfect place to un-wine-d, you don’t have to dip into your vino budget for an amazing spot to stay. Thanks to Hotwire Hot Rate Downtown Chicago winery hotels deals, you can secure a top-shelf hotel for cheap Downtown Chicago hotels prices.

Drinking in the Good Times in Downtown Chicago

The ultimate in vacay bliss? You, relaxing in your Downtown Chicago winery hotel after a fantastic day of wine tasting and vineyard strolling. This doesn’t have to be pinned away on your “one day” bucket list—booking a Hotwire Hot Rate hotel deal can make this primo daydream a reality. And for way less than you expected. The biggest dilemma you’ll have to face on your Downtown Chicago getaway is red, white, or rosé?

Frequently Asked Questions About Winery Hotels

How to get last-minute deals on winery hotels in Downtown Chicago?

Scoring a fantastic Downtown Chicago winery hotel deal is as easy and breezy as a glass of Riesling on a summer’s day when you book a Hotwire Hot Rate hotel deal, even if you wait until the last minute. Because you could save up to 60% off versus booking a listed rate two weeks earlier with Hotwire’s last-minute deals. And with hotels as low as $119, you don’t have to worry about the cost of your stay sipping into your bottle budget. Cheers to the very best deals on Downtown Chicago winery hotels.

How many winery hotels are in Downtown Chicago?

With 1,621 Downtown Chicago winery hotels to choose from, you’re sure to find a spot to please your picky palate. Especially when you can count on finding some of the best places to stay in Downtown Chicago ready for the picking with Hotwire Hot Rate deals. Four-star hotels at 2-star prices? That calls for a celebration. Good thing there’s sure to be something sparkling nearby.

How to find cheap winery hotels in Downtown Chicago?

Booking cheap winery hotels in Downtown Chicago is a simple task. Check out all of the best and bubbly deals available, and then choose which spot best suits your tastes. When you pick a Hotwire Hot Rate hotel deal you won’t know the exact hotel name until after you’ve booked, but know that you’ll soon be toasting to your impeccable money-saving skills and the sweet spot you just scored.

Is it safe to travel to Downtown Chicago during the coronavirus (COVID-19) crisis?

With the most recent COVID-19 closures and reopenings, you may be wondering is it safe to travel to Downtown Chicago right now. When booking your last-minute getaway to Downtown Chicago winery hotels, make sure to check out the latest information on safety measures, closures, and up-to-date guidance on traveling during the coronavirus.